Step 1: Prep the Oven and the Topping
Preheat your oven to 350°F (175°C). Pour the ¼ cup of melted unsalted butter directly into your 9-inch pan or cast-iron skillet, swirling it around to ensure the bottom is entirely coated. Sprinkle the ½ cup of packed dark brown sugar evenly over the melted butter. This sugar-butter mixture is going to bubble and transform into your glorious caramel glaze as it bakes in the oven.Step 2: Arrange the Tropical Fruit
Take your drained pineapple rings and pat them relentlessly with paper towels until they are entirely dry. Arrange one ring dead center in the pan, on top of the brown sugar. Place the remaining rings in a circular pattern around the center ring. You can cut a few rings in half to line the outer edges if there are gaps. Place a drained maraschino cherry right in the center hole of each pineapple ring, and fill any remaining empty spaces with extra cherries. Set the pan aside.Step 3: Whisk the Dry Ingredients
In a medium-sized mixing bowl, thoroughly whisk together the 1 ½ cups of all-purpose flour, baking powder, baking soda, and fine sea salt. Whisking aerates the dry ingredients and ensures the leavening agents are distributed evenly, preventing any large, bitter holes or uneven rising in your baked sponge.Step 4: Cream the Butter and Sugar
In the main bowl of your stand mixer fitted with the paddle attachment, beat the softened ½ cup of butter on medium-high speed for 1 minute until creamy. Add the ¾ cup of granulated sugar and continue to beat for a full 3 to 4 minutes until the mixture is pale, airy, and noticeably fluffy. This crucial creaming step forces microscopic air bubbles into the fat, dictating the ultimate lightness of your crumb.Step 5: Emulsify Eggs and Flavorings
Reduce the mixer speed to medium-low. Add the room-temperature eggs one at a time, allowing each to fully incorporate and emulsify before adding the next. Stop to aggressively scrape down the sides and bottom of the bowl with your silicone spatula. Pour in the pure vanilla extract and blend until the batter is smooth and cohesive.Step 6: Alternate the Wet and Dry Ingredients
In a small liquid measuring cup, combine the ⅓ cup of whole milk and the 2 tablespoons of reserved pineapple juice. Turn the mixer to its lowest speed. Gradually add the whisked dry ingredients in three parts, alternating with the milk mixture in two parts (Flour -> Milk -> Flour -> Milk -> Flour). Mix only until the last streaks of flour disappear. Overmixing here develops gluten and will make your final dessert tough and rubbery.Step 7: Pour, Bake, and Execute the Perfect Invert
Carefully spoon the thick batter over the arranged fruit in your skillet or pan. Use an offset spatula to gently spread it into an even layer, being highly careful not to shift the fruit arrangement underneath. Bake for 40 to 45 minutes, or until a wooden toothpick inserted into the center comes out entirely clean.
